Two new compounds from the fruit of <i>Ailanthus altissima</i>

Ni, Jian-Cheng; Shi, Jianting; Tan, Qing-Wei; Chen, Qi-Jian

doi:10.1080/14786419.2018.1437434

Cited by 14 publications

(12 citation statements)

References 25 publications

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“…The ES extract was subjected to a series of chromatographic columns including Sepabox for separation, purification, and isolation. After using various spectroscopic techniques and literature comparison, we identified the isolated compounds to be syringaresinol ( 1 ) ( Koul et al, 2016 ), syringin ( 2 ) ( Ni et al, 2019 ), and (−)-epicatechin ( 3 ) ( Fan et al, 2018 ) ( Fig. 1 ).…”

Section: Resultsmentioning

confidence: 99%

Compounds isolated from Euonymus spraguei Hayata induce ossification through multiple pathways

Imtiyaz

Lin

Cheong

et al. 2020

Saudi Journal of Biological Sciences

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The process of bone metabolism includes catabolism of old or mature bone and anabolism of new bone, carried out by osteoclasts and osteoblasts respectively. Any imbalance in this process results in loss of bone mass or osteoporosis. Drugs available to combat osteoporosis have certain adverse effects and are unable to improve bone formation, hence identifying new agents to fulfil these therapeutic gaps is required. To expand the scope of potential agents that enhance bone formation, we identified Euonymus spraguei Hayata as a plant material that possesses robust osteogenic potential using human osteoblast cells. We isolated three compounds, syringaresinol ( 1 ), syringin ( 2 ), and (−)-epicatechin ( 3 ), from E. spraguei. Results demonstrated that syringin ( 2 ), and (−)-epicatechin ( 3 ), increased alkaline phosphatase activity significantly up to 131.01% and 130.67%, respectively; they also elevated mineral deposition with respective values of up to 139.39% and 138.33%. In addition, 2 and 3 modulated autophagy and the bone morphogenetic protein (BMP)-2 signaling pathway. Our findings demonstrated that 2 and 3 induced osteogenesis by targeting multiple pathways and therefore can be considered as potent multi-targeted drugs for bone formation against osteoporosis.

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Section: Resultsmentioning

confidence: 99%

Compounds isolated from Euonymus spraguei Hayata induce ossification through multiple pathways

Imtiyaz

Lin

Cheong

et al. 2020

Saudi Journal of Biological Sciences

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“…Pharmacological and clinical investigations have revealed that C 20 quassinoids from Ailanthus genus plant are very promising for their medical use, such as antitumor, antimalarial, antiviral, antiparasitic properties etc. [4][5][6]. We have previously reported the identification of eighteen C 20 quassinoids including nine new quassinoid glycosides, named chuglycosides A-I, from the samara of A. altissima.…”

Section: Discussionmentioning

confidence: 99%

“…Swingle, a Simaroubaceae plant native to China and widely distributed in North America and European countries [1,2], have been extensively used in traditional Chinese medicine for the treatments of ascariasis, bleeding, spermatorrhea, diarrhea and gastrointestinal diseases [3]. The extract of the plant has been reported to possess a broad range of bioactivities such as antitumor, antimalarial, antiviral, antiparasitic, herbicidal and insecticidal properties [4][5][6]. Phytochemical investigations have reported the characterization of quassinoids, β-carboline alkaloids, triterpenoids, coumarins, phenylpropionamides, piperidine, and phenolic derivatives [7][8][9][10][11][12], etc.…”

Section: Introductionmentioning

confidence: 99%

“…Phytochemical investigations have reported the characterization of quassinoids, β-carboline alkaloids, triterpenoids, coumarins, phenylpropionamides, piperidine, and phenolic derivatives [7][8][9][10][11][12], etc. We have initiated a phytochemistry study on the samara of A. altissima, and previously we have reported the identification of 58 natural products of diverse structures such as quassinoids, coumarins, flavonoids, phenylpropanoids, phenylpropionamides, piperidine and phenolic derivatives, among which were a series of novel compounds including nine quassinoid glycosides, two phenylpropionamides, one piperidine, one terpenylated coumarin and two phenolic derivatives [5,7,13]. In this paper, we report the purification and identification of another two novel quassinoid glycosides, named chuglycosides J (1) and K (2), which were isolated from the A. altissima samara during our ongoing studies, together with fourteen known lignan and neolignans including tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxyphenyl) methyl]-3-furanmethanol (3) [14], (+)-lariciresinol (4) [15], (+)-(1R,2S,5R,6S)-2,6-di(4 -hydroxyphenyl)-3,7-dioxabicyclo [3.3.0]octane (5) [16], (+)-pinoresinol (6) [17], (+)-isolariciresinol (7) [18], (+)-isolariciresinol 3α-O-β-glucopyranoside (8) [19], burselignan (9) [18], densispicoside (10) [20], secoisolariciresinol (11) [15], dehydroconiferyl alcohol (12) [21], curcasinlignan B (13) [22], erythro-guaiacylglycerol-β-O-4 -coniferyl ether (14) [23], 7R,8R-threo-4,7,9,9 -tetrahydroxy-3,3 -dimethoxy-8-O-4 -neolignan (15) [24], threo-2,3-bis-(4-hydroxy-3-methoxyphenyl)-3-methoxypropanol…”

Section: Introductionmentioning

confidence: 99%

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Two Novel Quassinoid Glycosides with Antiviral Activity from the Samara of Ailanthus altissima

Tan

Shi

et al. 2020

Molecules

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Phytochemistry investigations on Ailanthus altissima (Mill.) Swingle, a Simaroubaceae plant that is recognized as a traditional herbal medicine, have afforded various natural products, among which C20 quassinoid is the most attractive for their significant and diverse pharmacological and biological activities. Our continuous study has led to the isolation of two novel quassinoid glycosides, named chuglycosides J and K, together with fourteen known lignans from the samara of A. altissima. The new structures were elucidated based on comprehensive spectra data analysis. All of the compounds were evaluated for their anti-tobacco mosaic virus activity, among which chuglycosides J and K exhibited inhibitory effects against the virus multiplication with half maximal inhibitory concentration (IC50) values of 56.21 ± 1.86 and 137.74 ± 3.57 μM, respectively.

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“…Terpenylated coumarins of interest for some age‐related disorders have been characterized (Dao et al, 2012). Antiviral coumarin derivatives were also isolated from the fruits of the plant (J. C. Ni, Shi, Tan, & Chen, 2017, 2019). But AIT is the best known bioactive secondary metabolite isolated from A. altissima , somewhat neglected after its discovery more than 50‐years ago but importantly revived in recent years with the discovery of significant anticancer effects.…”

Section: Introductionmentioning

confidence: 99%

Anticancer properties and mechanism of action of the quassinoid ailanthone

Bailly

2020

Phytotherapy Research

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Ailanthone (AIT) is a quassinoid natural product isolated from the worldwide‐distributed plant Ailanthus altissima. The drug displays multiple pharmacological properties, in particular significant antitumor effects against a variety of cancer cell lines in vitro. Potent in vivo activities have been evidenced in mice bearing hepatocellular carcinoma, nonsmall cell lung cancer and castration‐resistant prostate cancer. This review focusses on the mechanism of action of AIT, notably to highlight the capacity of the drug to activate DNA damage responses, to inhibit the Hsp90 co‐chaperone p23 and to modulate the expression of several microRNA. The interconnexion between these effects is discussed. The unique capacity of AIT to downregulate oncogenic miR‐21 and to upregulate the tumor suppressor miRNAs miR‐126, miR‐148a, miR‐195, and miR‐449a is presented. AIT exploits several microRNAs to exert its anticancer effects in distinct tumor types. AIT is one of the rare antitumor natural products that binds to and strongly inhibits cochaperone p23, opening interesting perspectives to treat cancers. However, the toxicity profile of the molecule may limit its development as an anticancer drug, unless it can be properly formulated to prevent AIT‐induced gastro‐intestinal damages in particular. The antitumor properties of AIT and analogs are underlined, with the aim to encourage further pharmacological studies with this underexplored natural product and related quassinoids. Highlights Ailanthone (AIT) is an anticancer quassinoid isolated from Ailanthus altissima It inhibits proliferation and induces cell death of many cancer cell types The drug activates DNA damage response and targets p23 cochaperone Up or downregulation of several microRNA by AIT contributes to the anticancer activity Analogs or specific formulations must be developed to prevent the toxicity of AIT

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Two new compounds from the fruit of Ailanthus altissima

Cited by 14 publications

References 25 publications

Compounds isolated from Euonymus spraguei Hayata induce ossification through multiple pathways

Compounds isolated from Euonymus spraguei Hayata induce ossification through multiple pathways

Two Novel Quassinoid Glycosides with Antiviral Activity from the Samara of Ailanthus altissima

Anticancer properties and mechanism of action of the quassinoid ailanthone

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